Manufacture of strongly basic azodyestuffs



Patented Aug. 30, 1932 UNITED STATES PATENT OFFICE ACHILLE GONZETTI, FIBASEL, SWITZERLAND, ASSIGNOR TO THE FIRM: J'. R. GEIG'Y,

S. .A., OF BASEL, SWITZERLAND MANUFACTURE OF STRONGLY BASIC AZODYESTUFFSNo'Drawing. Application filed July 28, 1928, Serial No. 296,104, and. inGermany August 6, 1 927.

The present invention relates to the manufacture of strongly basicazodyestuifs and consists in converting'an azo component of the benzeneseries capable of being coupled,

by successive treatment with chloracetylchloride and an alkylamine ofthe fatty series, into a basic body of the general formula:

R-NH -G O-GHz-NEB,

wherein R represents a radical of the benzene or naphthalene seriescontaining a free amino group and B represents hydrogendialkyl groups ortrialkyl groups, diazotizing the body thus obtained and coupling same toan azo component of the benzene and naphthalene series. Suchtransformation into a strong basic body of the kind above referred tocan take place by operation on the starting azodye component, or on amiddle component, if it be used for diazotizing purposes, or on thefinal azodye component, or on two or more of such components at a time,in so far as that at least one of the azodye components to be coupledfor obtaining the desired azodyestuffs is converted 'into a basic bodycontaining the group above referred to.

Any alkyla-mine of the fatty series can be employed to the effect statedabove; however, dialkyland trialkyl-amines of the fatty series arepreferred. Thus, for example, dimethylamine, diethylamine,trimethylamine and so on can be used.

The following example illustrates the process:

E wampZe.-21.l kilos of chloracetyl-metanitraniline are introduced into43 kilos of commercial dimethylamine solution of 23.3 per cent,strength. This mixture is heated gently for-2 hours at 60 0., thenthoroughly 7 cooled and filtered. The crude product is dissolved in 200litres of boiling water acidi- .fied with hydrochloric acid and thesolution filtered. On cooling there is obtained in satisfactory yieldthe hydrochloride of dimethylamine-acetyl-amino-meta nitraniline in theform of white crystals of melting point 236 C. of the probable formula:

CH3 NHC OCH2NCHs 26 kilos of this nitro-product are reduced by means ofiron and acetic acid in known manner. The reduction liquor is diazotizedby means of 30 kilos of concentrated hydrochloric acid and 6.9 kilos ofsodium nitrite. The mineral acid is neutralized by means of sodiumacetate and more crystallized sodium acetate is added to the amount ofkilos, and into this diazo-solution, is run one of 14.4 kilos ofbeta-naphthol in 200 litres of water and 13 kilos of caustic soda lye ofper cent. strength.

The dyestuif is completely precipitated. It dyes a pure orange red ontannin-morda'nted cot-ton and an orange of good fastness to washing andlight on weighted silk.

In tbis'example, any other azodye component canbe rendered stronglybasic by the method above described. Thus the process can be applied tochloracetyl-para-nitraniline, ohloracetyl-2:7-amidonaphthol, chloracetylethyl p ara nitraniline, chloracetylnitro-ortho-anisidine and so on.

The products obtained yield by coupling with any usual azo component,such as betanaphthol, phenylenediamine, meta-toluidine etc. usefulazodyestuffs dyeing tanning-mor danted cotton, weighted silk and thelike good tints of great fastness to washing and light. I

What I claim is:

1. A process for the manufacture of strongly'bas'ic azodyestulfs,consisting in conspyonnaphthalene series containing ,a free said,azodyestufis dyeing tannin'l-mordanted.

verting an azo component of the benzene se- 7 ries capable of beingcoupled, by successive treatment with chloracetyl-chloride and analkylamine of the fatty series, into a basic body of the general'formulaR-NH-OO-OHPNEB,

wherein R represents a radical of the benzene or naphthalene seriescontaining a free aminogroup and B represents hydrogen-d1- cotton,Weighted silk and the like good tints of great fastness to washing andlight.

In witness whereof I have hereunto signed a 'my namethis 16th dayofJuly, 1928. e

ACHILLE CONZETTI.

alkyl groups or trialkyl groups, 'diazotizing the body thus obtained andcoupling same to an azo component of the benzene and naphthalene series.Y

strongly basic azodyestufls, consisting in converting an azo componentof the benzene I nent of the benzene and naphthalene series.

"of the fatty I series capable of being coupled, by successive 1 whereinR represents a radical of the benzene or naphthalene series containing afree aminogroupand B represents hydrogen-di- Lalkyl groups, diazotizingthe body thus obtained and coupling same to anazo compoprocess for themanufacture; of l Q 3. Aprocess for the manufacture of stronge 1y basicazod'yestufls, consisting in converting an azo component ofthe benzeneseries capableof being coupled, by successive treatment withchloracetyl-chloride and dimethylamine general formula 1 0Hiv i 1wherein R representsa radicalof thebenzene .or naphthaleneiseriescontaining a free aminogroup, diazotizing the body thus ob-v '7 series,into a basic body of the tained'and coupling same to an azo com: o

ponent of the benzene and naphthalene series. ie-As new articles; ofmanufacture, the, strongly basic azodyestuifs obtained by the useof anazo component of the benzene series converted by successive treatmentwith chloracetyl-chloride and an alkylamine of the fatty mula V series,into a basic'body of the general 013 whereinR representsa radical of thebenzene amino-group and B represents hydrogen-di- 7 alkyl groups ortrialkyl groups, diazotization of such body and its coupling to an azocomponent of the benzene and naphthalene series,

